Thio­phene-2-carbaldehyde 2,4-dinitro­phenyl­hydrazone

Zhi-gang Yin; Heng-yu Qian; He-ping Li; Jie Hu; Chun-xia Zhang

doi:10.1107/S1600536808038397

. 2008 Nov 22;64(Pt 12):o2421. doi: 10.1107/S1600536808038397

Thiophene-2-carbaldehyde 2,4-dinitrophenylhydrazone

Zhi-gang Yin ^a,^*, Heng-yu Qian ^a, He-ping Li ^b, Jie Hu ^a, Chun-xia Zhang ^a

PMCID: PMC2959885 PMID: 21581389

Abstract

In the approximately planar molecule of the title compound, C₁₁H₈N₄O₄S, the dihedral angle between the thiophene and benzene rings is 5.73 (10)°. In the crystal structure, bifurcated inter/intramolecular N—H⋯(O,O) hydrogen bonds are present. The intermolecular links lead to inversion dimers containing an R ₂ ²(12) graph-set motif.

Related literature

For general background, see: Okabe et al. (1993 ▶). For graph-set notation, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₁H₈N₄O₄S
M _r = 292.27
Monoclinic,
a = 4.8994 (17) Å
b = 9.520 (3) Å
c = 25.708 (8) Å
β = 92.71 (2)°
V = 1197.7 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 291 (2) K
0.30 × 0.26 × 0.24 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T _min = 0.915, T _max = 0.929
11010 measured reflections
2285 independent reflections
1718 reflections with I > 2σ(I)
R _int = 0.047

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.087
S = 1.02
2285 reflections
184 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808038397/dn2406sup1.cif

e-64-o2421-sup1.cif^{(17.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808038397/dn2406Isup2.hkl

e-64-o2421-Isup2.hkl^{(112.3KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1⋯O1ⁱ	0.87 (2)	2.57 (2)	3.338 (2)	148.2 (19)
N3—H1⋯O1	0.87 (2)	2.01 (2)	2.630 (2)	127.4 (19)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors express their deep appreciation to the Startup Fund for PhDs of Natural Scientific Research of Zhengzhou University of Light Industry (grant No. 2005001) and the Startup Fund for Masters of Natural Scientific Research of Zhengzhou University of Light Industry (grant No. 000455).

supplementary crystallographic information

Comment

2,4-Dinitrophenylhydrazine is a reagent which is widely used for condensation with aldehydes and ketones. Several phenylhydrazone derivatives have been shown to be potentially DNA-damaging and are mutagenic agents(Okabe et al. 1993). As part of our work, we have synthesized the title compound (I) and reported its cyrstal structure.

The title molecule is roughly planar. Indeed, the benzene and the thiophene rings are only slight twisted, making a dihedral angle of 5.73 (10)° (Fig. 1). The two nitro groups, O1/N1/O2 and O3/N2/O4 are coplanar with the benzene ring to which they are attached.

Intermolecular N-H···O hydrogen bonds link the molecule two by two around inversion center, building then a R₂²(12) graph set motif (Etter et al., 1990; Bernstein et al., 1995) if the intramolecular N-H···O hydrogen bonds are ignored (Table 1, Fig.2).

Experimental

2,4-dinitrophenylhydrazine(1 mmol, 0.198 g) was dissolved in anhydrous methanol, H₂SO₄ (98% 0.5 ml) was added to this, the mixture was stirred for several minitutes at 351 K, thiophene-2-carbaldehyde (1 mmol 0.112 g) in methanol (8 ml) was added dropwise and the mixture was stirred at refluxing temperature for 2 h. The product was isolated and recrystallized in methanol, purple single crystals of (I) was obtained after 5 d.